


Angelic Trickster Over Backstabbing Demons, Every Time

by thefandomsinhalor



Category: Supernatural
Genre: Alternate Universe - Canon Divergence, Angst, Demon Blood, Hurt/Comfort, I'll add tags as I go along, M/M, Post-Season/Series 03, Protective Gabriel, Season/Series 04, Time Travel, Trickster Gabriel (Supernatural)
Language: English
Status: In-Progress
Published: 2019-06-07
Updated: 2019-07-12
Packaged: 2020-04-12 11:20:55
Rating: Not Rated
Warnings: Graphic Depictions Of Violence, Major Character Death
Chapters: 2
Words: 9,169
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19131001
Author URL: https://archiveofourown.org/users/thefandomsinhalor/pseuds/thefandomsinhalor
Summary: Desperate and lost after Dean was sent to hell, Sam is trying to survive and do something productive instead of going insane. His options are limited and Ruby's offer to take down Lilith appears to be the best he's got.That's when a tricky visitor shows up and proposes an alternative solution containing many revelations about Sam's past, present and future.





	1. An Unexpected Visitor

Sam was desperately scrubbing the blood off his hands. Even though he hadn’t bothered turning on the bathroom light, he purposely avoided looking in the mirror in front of him while doing so.

Unable to know with certainty if everything was washed off, he continued a little longer once he felt his hands stinging.

He then poured cold water on his face quickly, hoping he would get most of it off as well, before finally turning off the water tap.

Exhausted, and his legs almost giving out when he reached the doorway, he still managed to get himself to the bed without completely falling over.

The bed was hard and small, but it would do. There weren’t many details regarding his well-being that Sam cared about these days.

On his back and ready to pass out, he then grunted in frustration at the bright light shining over him.

It was too bright. Even with his eyes shut it was bothering him. He contemplated getting up to fix his discomfort.

But he stayed put. Stillness was helping. He felt too heavy for anything else. Sleep was what he needed, he decided.

Sleep. So he could forget everything.

But soon enough images of Dean dying in his arms, bloody and too quickly, popped up again.

They always did.

Dean screaming.

Dean being torn to shreds.

And Sam not being able to do anything but watch.

He opened his eyes, panic rising in his chest.

_No, not sleep. Not this again._

He sat up quickly, fighting tears.

He glanced hopelessly at the empty motel room he was in. Considering he was in a place where plumbing was available, it was a huge upgrade from the run down places he had been hiding out lately.

He couldn’t even remember why he’d bothered getting a room at all.

Because nothing else mattered anymore.

He wrapped his fist around Dean's necklace, with a heavy heart.

_I don’t know what I’m supposed to do, Dean._

_I want to help you, but I don’t know how._

_Please._

_Someone._

_Help me. Help me help him._

But nothing.

No one could help him.

Not even Ruby.

Or her insane plan of action she had suggested to him.

Psychic powers or not, this still didn’t solve Dean’s urgent location issue.

None of this was giving him his brother back and out of hell.

And it wasn’t because he hadn’t tried.

But without success.

So his options were to either stop obsessing about Lilith and to continue the good fight—the good fight that had brought Dean to his death, as well as nearly everyone he ever cared about—or to think outside the box by sticking to Ruby’s offer and perhaps do something seemingly more productive.

Not exactly the option he wished for, especially when her methods were concerned, but it wasn’t nothing.

“I’ll still tag along with her,” he decided.  “What else do I have to lose?” He lowered his eyes, and then clumsily grabbed the half empty bottle of whiskey resting by the bed.  He took a swig, before dropping it on the floor again. He let out a deep sigh and ran his hand over his face in a poor attempt to wake himself up.

“Oh, Sam. Really?” said a voice. “Seeing you like this is—well, I want to say déjà vu but that’s not even funny anymore. Don’t tell me I put you through this hell for nothing?”

The trickster had suddenly appeared in his motel room and was resting comfortably in one of the armchairs facing the bed.

“You!” Pulling a knife, Sam jumped to his feet, ready to slice him.

“Relax. I come in peace.” The trickster calmly waved his hand to left and the knife instantly disappeared.

Sam reached for his bag on the other side of the bed, but it flew into the wall the moment he was about to reach for it.

“I said, I come in peace.” The trickster had his hands up in the air, not moving from his spot. “Besides, it’s not like any of this stuff would actually harm me anyway. You know that.”

Unarmed and frustrated, Sam yelled, “You! You son of bitch.” He staggered towards him as best as he could, but found himself gently nudged back on the bed.

“I think it’s best if you stay put, Sammy,” he said, not having moved a muscle.

“You—you—how—let me go!!” Desperate to move, Sam was fighting against an invisible force keeping him still.

“Calm down and maybe I will.”

“I’m going to tear you apart, you piece of—”

“That’s a tad harsh, but okay.” Sam was still restless and shot him angry looks. “So much aggression. How about we move on?”

Sam let out of laugh while stubbornly trying to free himself.

“I thought we had,” said the trickster in a genuine voice. “Moved on, I mean. Clearly I was wrong.”

“Big time. And you’re going to pay for what you did.”

“That’s unfortunate, considering what I’m here for.”

Frustrated, Sam groaned and finally stopped moving.

“What the fuck do you want? Why are you here?”

“I’m here to help you.”

“Haha. Right, pass. I’ve seen how you help.”

“Okay, that was—harsh love. Slightly misguided, perhaps, but still well meant. I’ll come back to that. But no. No tricks this time.” Sam frowned at him. “Just the truth.”

“No tricks? Said the trickster. Sure.”

“Ugh. Okay, first off, not a trickster.”

Sam stared at him, seemingly indifferent.

“What are you then?”

He sighed. “Um, if we are going to have a big discussion, I need you focused and…well, here.” He stood up, and after a few steps, he gently bopped Sam on his forehead. Sam froze, nearly dreading whatever horrific thing he could have done to him. But nothing happened. Nothing had changed.

And then he felt it.

His heaviness. His spinning head. His hazy mind.

Gone.

Anger. Pain. Confusion.

Feeling defeated and helpless.

He looked at the trickster with worry.

“Better than a banana bag at the hospital, I can tell you that,” he said, still standing.

“You sobered me up?”

“In a way. Yes.”

“Why?”

“I told you, we need to talk and I want you alert.”

“No. I don’t think so. This is just another one of your tricks. _Trickster._ ”

“I also told you, not a trickster.”

“Then what?”

He bit on his lip, then took a deep breath while looking upwards and said, “One crazy bomb at a time. I’m here hoping I can help you—”

“Pass.”

“—with Dean.”

Sam flinched. He held his breath and scanned the man’s face intensively. “You’re lying.”

“I am not,” he said, sounding almost jolly, as he took his seat back.

 Sam stared at him. He swallowed and his heart beat fastened. He urgently shook his head, refusing to let himself be duped. And with a quick wave of a hand, Sam was no longer held back, freed from the invisible restrain.

But he remained seated.

“Why would you care about what happened to Dean?”

“I actually care a whole lot.”

“Really? Didn’t look that way to me when you killed him and made me watch it over a hundred times.”

The trickster bit on his lip again and looked down. “Like I said before, tough love.”

Sam shook his head. “No. This is what you wanted: Dean dead.”

“It is absolutely not.” This time his voice hadn’t been calm or even peppy. His stern look and clenched jaw told Sam that he had offended the trickster by his accusation. “This is not what I wanted,” he repeated.

“Then why didn’t you do anything? If you supposedly can help me—us, which I doubt, why didn’t you do something when you could have instead of waiting until now.”

“I couldn’t.”

“BUT YOU JUST SAID—”

“Sam,” he said, lifting his hands in protest. For half a moment, Sam thought he had frightened him. An uneasiness had appeared in his eyes, but vanished the instant he had barely assessed it. “Dean dying and going to hell, that’s not what I wanted. It was something I just couldn’t stop. That’s the difference. I was trying to—” he started to say, but stopped himself. He took a deep breath and repositioned himself on his chair. “The important part that you need to understand is that I couldn’t do anything then, but I could potentially do something now.”

Sam surveyed him.

_What if…_

_What if it’s true?_

_What if it’s a trap?_

_It’s definitely a trap._

He huffed. “No, it can’t be—you’re lying. I—I have tried everything, everything I could think of. And above. Even demon deals. There’s nothing.”

“There are other beings far better and more powerful than demons, Sam.”

“You’re saying they’re not powerful?”

“Oh no. That, they are,” he said grimly. Sam frowned as he noticed the trickster shaped his hand into a fist. “But my point is that you’re looking at it the wrong way. As you’re supposed to be.” 

“What is that supposed to mean?”

But the trickster remained silent.

Sam held his stare and thought for a moment. He could feel his anger boiling and spreading throughout his body.

_But what if..._

“Okay, either you tell me what’s what right now or get out.”

He sighed. “Don’t worry about Dean, he’ll be back.” At the sight of Sam, who was clearly upset and ready to throw a rampage of angry words at him, he urgently added, “Of course, there is cause for concern giving where he is, but I just  mean that it will work out in the end.”

“How do you know?”

“I just do.”

Sam stared at him.

“Dean’s going to come back?”

“Yes.”

“And he’ll be okay?”

“He’ll adjust, but eventually, yes.”

“How?”

“Just—it will happen.”

“But how? You’re going to help me get him out?”

“No, not me. _We_ aren't the ones who will.”

“Then who?”

The trickster shook his head, refusing to answer's Sam's question. “You’ll just have to take my word for it.”

Sam examined him, trying to spot any indication that he was mocking him.

“Even from you, that’s pretty cruel to give me false hope like that.”

“It isn’t false hope. It’s just what is going to happen. Goodness, is it me, or are you a little slower than usual? Did I not put you back together right, earlier? Stop repeating everything I’m telling you.”

“If Dean gets out of hell,” continued Sam, ignoring him, “but neither of us are the one helping him, and I have no play into it, then why are you telling me at all? Besides the potential—sort of—relief it’s giving me, how are you _helping_ me? That’s what you said, right? Helping me?”

“Oh no,” he said waving his hand, in protest. “That’s not how I will help you. _That_ was the introductory. I’m here to help you with Dean. For _after_ he comes back. And in order to do that, we have to deal with Ruby. I’m here to keep the situation with Ruby in check.” He tilted his head and added, “Sort of.”

Sam's whole body tensed at the mention of Ruby’s name. With the events of the night tumbling through his mind, Sam felt his stomach dropped.

“I know she’s a demon, but she’s not bad,” he said, defensively. “Not really. She’s helped me a lot. She’s trying to.”

The trickster observed Sam for a moment, with tender eyes. “Sammy. Were you always this adorable? I mean, look at you. You haven’t even grown into your hair yet.”

“I’m not that naïve if that was your point,” he said, shrugging and then added under his breath, “Whatever that was.”

The trickster smiled. “Not that I want to be super discriminatory here, but they’re demons, Sam. That’s usually a really bad sign. For a reason. There’s only one I know of that isn’t too bad. One. Maybe two, but personally I have reservations about the second one. But that’s it. One in a million. ”

“You know a lot of demons?”

“I’ve—I’ve met one or two, yes.” He cleared his throat.

“And I shouldn’t trust her because of that reason alone?”

“You shouldn’t trust her because I know for a fact that she is playing you and will betray you.”

“ _Her_ playing _me_?” he asked, frowning. “That’s _your_ thing. And I can’t believe I’m about to say this, but so far, Ruby has been the only one to help me out. God, I’d even go so far as to say that she kind of looks out for me. Not that she needs to.”

“I bet she has been working really hard to make it seem like that, yes. But Sam, she’s not helping you. She’s not working for the same team. She’s deep in the game and she has you exactly where and how she needs you. Vulnerable. And alone. She’s manipulating you.” 

“Unlike you, you mean?" he scoffed. "And funny how she didn’t even bother trying to give me the ‘Dean will come back from the dead’ lie.”

“It’s not a lie, and you know I’m right about her. You know how? Because Dean was against it. Using your powers. What she’s suggesting, what she’s making—you don’t even know the whole thing yet, Sam, and even then you still know Dean was against it and for a good reason.”

“Yeah? Well, Dean not’s here. And maybe if I would have listened to Ruby before—”

“Oh, you would have stopped it?” he said, leaning forward in his seat, his elbows resting on the arms of the chair. “Cancelled Dean’s trip to hell? Sam, there was no stopping this. I told you. That’s one thing nobody could have stopped. But don’t you see, that’s how she gets to you. That Dean, despite all his good intentions and playing by the rules—most of the time—is now in a place that nobody wants to be. What better time could there be for her to take the opportunity to nudge you towards the freaking path you’ve been resisting all this past year?”

“But Lilith—Dean will want revenge.”

“You don’t know what Dean will want. You’d be surprised. But what he will _need_ , what you will both need, is each other. You two co-dependent lovable knuckleheads need each other.”

Sam remained silent, but the trickster could tell that he wasn’t overly convinced. Sinking himself back into the chair, he sighed and tapped on the arm of the chair, thinking. That's when Sam noticed for the first time that he was wearing a ring with a dark stone on his left hand. Puzzled, he frowned, not remembering the trickster wearing any kind of jewelry on their previous encounters. The trickster, realizing what Sam was looking at, slid off his hand from the arm of his seat onto his thigh,  evidently hoping to hide the ring.

He cleared his throat, and continued. “There’s much more at stake, but for now, let’s cut it down to this, Sam. Which one do you prefer: getting Dean back—really getting Dean back, I don’t just mean from hell, but on your side and his trust never failing once—or getting your vengeance on Lilith? Because I’m here to tell you that Dean will be back no matter what, so going after Lilith is pointless. And if you do this, if you side with Ruby on this, that’s going to screw things up for you both in so many ways you can’t even imagine, and that’s including a rift between you and Dean.”

“How could you possibly know any of this?”

“Because I know what’s going to happen, Sam,” he said, a tentative smile on his face. But it quickly vanished as he continued, “And I don’t like where it’s heading. For either of us. For a lot of people. The world gets saved, for a while at least, so yay team. But it never really stays that way. And I’m not gonna lie, it’s ugly. It’s pain and torment. Years of it. Over a decade of torment. For the both of us. And Dean. And Cas.”

“Who’s Cas?” asked Sam, frowning.

“Right. Getting ahead of myself here. The point is, I know what will happen. I know which dominoes needs to fall to create certain waves, and which ones to avoid.”

“How do you know any of this?” Sam asked him again.

“I’m nosy. It’s kinda my thing,” he said, amused.

But there had been something else in his tone that had left Sam doubtful of his statement.

Sam pursed his lips. “Really, though. How?” He sat there waiting for an explanation but the trickster only smiled at him. Not mischievously, but rather, with a genuine smile.

Finally, he said, “I’ll leave you for now to mull things over. I would suggest you keep our little chat to yourself. No sharing with Ruby.” He glanced quickly around, as if he was looking at something invisible to Sam's eyes, and said, “I think I set up the room right. You should be fine until next time.”

Still seated in his armchair, he was then suddenly holding an old fashion glass, filled with a brown liquid. “One for the road. Cheers,” he said lifting his drink, as he winked at Sam. He took a swig from it, and put down the glass on the table by the side of the armchair.  The drink was then half full. “I’ll be around and keep an eye on you. I’ll return when you’ll be ready to hear some more.”

“Wait,” pressed Sam. “Before you go, please, can you at least tell me one thing?”

“What?”

“How does Dean get out of hell? And when?”

“He gets out soon. But you have to wait a little longer.”

“But how?”

He let out a short laugh. He observed Sam for a moment, weighing if he should share this information or not. Then a smile formed itself at the corner of his mouth, and he said simply, “An angel of the Lord rescues him.” He stood up from his armchair nonchalantly and fixed his jacket.

Sam rolled his eyes. “An angel of the Lord,” he repeated in a monotone voice.

“Yup.”

“Why would an angel of the Lord care enough to help my brother?”

“A story for another time.”

Sam stared at him, and then nodded, snorting. “How stupid do you think I am? Angels don’t exist.”

“Hmm. Consider my feelings hurt. You’re speaking to one right now.”

“You’re an angel,” he said, squinting. He sighed, lifting his eyes at the ceiling, annoyed. “Okay,” Sam grinned at him. “What’s your name?” he asked, returning his eyes on him.

The man smiled warmly, as if remembering a fond memory, and said, “Gabriel. They call me Gabriel.”

Sam held his breath as the expression of the other man wasn’t anything but truthful. “You mea—you mean like the—the archangel? Like the—now, I know you’re fucking with me.”

“Oh Sam, don’t give me ideas.” And he vanished right in front of Sam’s eyes with a whooshing sound, and Sam felt a strong breeze brush across his face.

 

An odd mixture of emotions was spreading within him when Sam woke up the next morning. At first, he wasn’t sure why, but he felt oddly hopeful. Something he hadn’t felt in a long time.

Then aggravation and worry rose in him.

And that was when he remembered.

The trickster.

_No, not a trickster._

_Gabriel._

He chuckled at the absurdity of it all.

_Maybe I should go easy on the booze next time because this is way past crazy, it’s just ridiculous._

_The trickster helping me._

_The trickster being an angel._

_An archangel._

_And an angel of the Lord to rescue Dean from hell._

Sam bit his lip.

 _And an_ angel of the Lord  _to rescue_ Dean  _from_ hell _…_

He shook his head in resistance to this insane hope, but he couldn’t help laying there and daydreaming about it.

_If that was real…which it probably wasn’t…_

_But even if it was…_

_For one second, let’s say it was, then what?_

Not that he fully trusted the so-called archangel—the Mystery Spot was still very vivid in his mind—but he had to admit that the idea of Dean coming back (and saved by an angel of the Lord no less) was both ridiculous and extraordinary.

Perhaps too extraordinary.

This sounded too good to be true.

Reflecting on the _dream_ encounter, however, one fact bothered Sam and he couldn’t ignore it. The truth was that even if he didn’t really like or trust the trickster, the idea that he wouldn’t need to rely on Ruby— and her, perhaps, questionable methods—revealed itself to be a great relief to him.

Dream or not, this was unexpected and worrisome because it proved one thing: he had hesitations about Ruby.

_That’s not surprising considering what actually happened the night before._

He lifted his hands and saw dried blood was still visible under his fingernails.

_I just have to get my head in the game._

Sam sighed and decided that he should simply forget about it.

It was just a dream.

A dream fueled by booze and despair.

He sat up, ran his hand in his hair and rubbed his face to help himself wake up. He was still sore from the fight the night before and the massive amount of whiskey intake wasn’t helping either. He should count his blessings that his head didn’t feel like it was split in two.

As he slowly and painfully made his way to the bathroom, however, he paused and glanced at the table where a half empty glass was resting at the same spot the trickster—Gabriel or whoever’s glass had been in his dream. Sam quickly scanned the room and found his own glass on his nightstand, exactly where he had remembered putting it.

He swallowed.

_It can’t be._

_That—that doesn’t mean anything._

_Just a coincidence._

_It has to be._

 

After he freshened up, he met Ruby at the empty warehouse like he was supposed to, but not before he took another look at the room, almost hoping his visitor would suddenly reveal himself.

But nothing happened. No surprise, there.

Ruby kept him busy, grilling him on their next move against Lilith. She had heard of a demon in the next town over with potential information and stated that this would be a good opportunity to continue his training as well. Two birds with one stone.

He did everything as usual. He listened to her. He weighed in on her plan. He tried everything she suggested.

But something was off.

His mind wasn’t in it.

His heart wasn’t in it.

Even if it had only been a dream, the notion that Ruby meant him harm was now implanted in his mind.

It wasn’t like he fully trusted her to begin with. But now, everything she said, everything she suggested, every nudge, smile or encouragement she gave him seemed false.

He questioned everything about her and there was no stopping it.

And unfortunately for Sam, Ruby noticed it and called him on it. When she demanded an explanation for his odd behavior, he found himself saying, “Ruby, do you think—do you know anything that could help Dean?”

She sighed, annoyed. “We’ve been over this, already. I’m sorry, Sam. But you know there’s nothing to be done. I don’t have the juice to do that. Nobody does.” She then watched him with attention, and added with a gentler voice, “But, like I told you, I can help you out with this. By bringing Lilith down.”

Not knowing what else to do, he nodded and he continued his day the best he could.

Ruby’s tip turned out to be a bust, and Sam was almost glad of it. Once that was settled, he didn’t lose any time telling her that he was calling it a day and that he needed to find a place to crash—alone—and rest.

If Ruby was upset or scorned by this, she didn’t let it show, but in that moment Sam didn’t care. He simply needed time to be on his own to think.

He also wanted to be away from Ruby.

 

Sam drove away in his car wearing protective charms so she wouldn’t find him. A few hours later, he stopped at a motel. He entered his room, dropped everything on the floor and got to work. He set up the usual deal of salt, devils traps and a few more charms to make sure Ruby or nobody else unwanted would get in. Or find him.

Satisfied that the room looked secure enough, he then sighed and said, “What now?”

He knew what he wanted to do, but he felt ridiculous just thinking about it.

He sat on the bed wondering how he was supposed to communicate with the trickster. He hadn’t mentioned that specific detail in his dream.

_I’ll be around and keep an eye on you. I’ll return when you’ll be ready to hear some more._

Discouraged, Sam shut his eyes.

That’s when suddenly an idea struck.

He felt silly, but he tried it anyway.

_Tricks—no._

_Gab—Gabriel?_

_Gabriel, this is Sam Winchester._

_I need your help._

_I need your ass—_

“My what, you say?”

_—istance._

Sam snapped his eyes open and gasped. Gabriel was standing right in front of him. Sam jumped on his feet and stepped back. 

“Holy shit, you’re real.”

“Again, what was that last one?”

“How did—you’re really…no, it can’t—”

“Um, Sam, you’re the one who called me. And speaking of which, I should probably give you my number or something because praying is a…let’s just say it’s an open line of communication. One that we should probably keep between us.”

Sam was simply gawking at him, so Gabriel felt the need to add, “But, never mind that for now. That’s just details for later.”

Remaining very still, and trying to keep his breathing under control, Sam was studying him with intensity.

“Sam? To what do I owe the calling?”

He took a deep breath and lifted his hand as a warning. “I’m not saying I believe you…”

“But?”

“But I’m ready to hear what you have to say. Tell me.”

“It’s kind of a long story.”

“Tell me the short version then,” he said, crossing his arms. “Talk. Why do angels care about Dean or me? How is Ruby playing me? And how do you know all this?”

“Angels don’t care: they are involved in this. And Ruby is not trying to help you bring down Lilith. She is trying to make you raise Lucifer bymaking you waste Lilith.”

Sam flinched in disbelief.

“And the reason why I know all this—how I know Dean will be rescued; how I know that Ruby will be one of your biggest troubles that will eventually cause issues between you and Dean and so much more; how I know all the pain that’s coming our way—is because I’m from the future, of course. I’m from the year 2018.”


	2. A Nightcap with Feelings

“You're from the future.”

“Yep.”

Sam was staring at Gabriel, dumbfounded.

“And you’re an angel.”

“Archangel, but correct again.”

He nodded absentmindedly. “An archangel from the future.”

“Sam? Blink twice if you’re still here.”

“You’re really going to make me say it?”

Gabriel shrugged. “Apparently,” he said as he sat on a chair.

“Prove it.”

“Okay, valid request,” said Gabriel, after letting out a small laugh, “but I can’t right now. Not the way you ask. And I’m also positive it wouldn’t be the best idea either.”

“Why?”

“I’ll get back to that one later on, but for now, can I just point out the fact that I am here at all, despite your…” He paused, gesturing at the room. Every window and door had been sealed with salt. And a panoply of sigils was on the floor and every wall of the room. And that was what was visible to the human eye. “Despite your room proofing,” continued Gabriel. “Very impressive, by the way. Not that many things could get in. And yet, here I am.”

Sam pursed his lips.

“If you allow me, however…” Gabriel stood up and rested one of his hands on the wall. Marks glowed briefly on the walls and then vanished all together. He stood back to look at his invisible handy work. “That ought to do it for now.”

“What was that?”

“Additional protection. Let’s call it an emergency cone of silence. Ish. Now the room is really secure.” He took back his seat. “That’s what I did yesterday in your other room when I visited.”

Sam was observing him carefully.

“If you have any questions, now is the time, Sam.”

“I have a lot of questions, but I’m…processing.”

“Understandable.”

“Have you always been from the future?”

“You mean, when we met and…after?”

“The Mystery Spot, yes.”

“No. That was me then. Now. You know what I mean.”

“So you just arrived from the future yesterday.”

“No. I didn’t just pop into your room last night directly from 2018. I arrived a few weeks ago. Then I laid low for a while.”

“What? Why?”

“Well, I’m—I’m surprised I managed to survive the trip at all. I knew if I made it, I would need to rest. I needed rest already anyway…” he said to himself, and then cleared his throat.

Sam shook his head. “I don’t understand. If you can travel in time, why did you do it—why now? Why stop here just to tell me about Dean coming back? Why didn’t you go back before he made the deal? Hell, why not—why not travel even before Jess—” Sam stopped mid-sentence, stood up and took a few steps away, his hands resting on his waist, and with his eyes fixed on the ground. “You obviously knew all of this in 2018 and if you chose—we could have avoided all of it.”

“As much as I would like this to be the case, Sam, I’m afraid it isn’t,” said Gabriel in a gentle voice. “Certain things couldn’t be avoided, not if we want to really make a change—a positive change—at the end of the day.” He scratched his head. “This is so much bigger than you think, and you and Dean are smack in the middle of it.”

Sam turned to him, with a stern look on his face, and after a moment, he asked, “How big?”

“Is the end of the world big enough?”

“Um, you mean like—like—you—”

“The Apocalypse, yes.”

“And that can be avoided by you coming here to me now…out of any other time?” he said, waving one of his hand in circle.

“Perhaps not _any_ other time, no,” he admitted, and then urgently added, “but I believe this one would ensure the best outcome in the long run, yes.”

Sam stared at him.

“Sam, listen—”

“Why is this the best time?”

Gabriel leaned back in his seat, sighing. “The short version? Because we’re close enough to the deadline now to do something about it and gather real players on our side, but it’s also still early enough so we’re not epically screwed.”

“And Dean going to hell doesn’t fall on the epically screwed list?” Sam clenched his jaw.

“Dean needed to go to hell.”

“Excuse me?”

“Yes, he did, and for two reasons. One, because that’s what the angels wanted. The high up ones, anyway," he added, more to himself than for Sam. “It was an important domino they needed to start the apocalypse. There was no stopping that. The best we could have done was to delay it, but then we would have lost some—”

“The angels want to start the apocalypse,” repeated Sam in disbelief, and cutting him off. “The angels, not the demons.”

“Oh, the demons are working that angle too. They’re just not aware they want the same thing, namely because both sides are idiots. They are convinced that they are in utter control of the situation, causing them to overlook other important stuff.”

“But—but wait—I thought you said an angel would be rescuing Dean from hell. Why would they want him to go to hell if they’re the ones yanking him out of there?”

“Because he needs to be there to break the s—” Gabriel stopped and looked upwards, huffing. “Okay, listen. I know it’s unfair, and I’m sorry, but this is like—you’re asking me to cover a lot of chapters in two seconds with explicit details and I can’t. I promise I’ll fill you in on the details later as best as I can, but for now I’ll give you the major plot points.”

Gabriel repositioned himself on his seat, took a deep, long breath and continued speaking after he quickly ran his fingers in his hair. “So as I was saying, Dean needed to go to hell because that’s what the angels and demons wanted. Want. Whatever—it's what they’ve been preparing for and expecting. If that doesn’t happen—let’s say because I would have intervened—that’s not something that would have been unnoticed. That’s not what I'm hoping for. I’m trying to shift this whole thing to our advantage, and our best bet is that I—we have to do this as subtly as possible.”

He gave Sam a moment to digest everything he had told him.

He observed Sam lost in his thoughts, reflecting on it all for a long while, until Sam lifted his eyes on him once more, and finally said, “What was the second reason? You said Dean needed to go to hell for two reasons.”

“Oh, that.” Gabriel beamed at him. “Well, um, if Dean doesn’t go to hell, then Cas never gets to save him from there.”

Sam frowned. “Wait, you said that name before. So Cas is—Cas is the angel who saves him?”

“That’s him,” he said, nodding firmly. “ _Castiel_ , to be more precise. And if Cas doesn’t save Dean, that means they don’t get their epic ‘I gripped you tight and raised you from perdition’ introduction. I mean, it wasn’t exactly a moonlight tryst, but it still worked for them,” he said, smirking.

Sam gaped. “A moonlight _what_ , now?”

“A tryst.”

Sam stared at him. “I know what a tryst—what?”

Gabriel smiled at him. “You’ll see. Fair warning though: they’re slow. And that’s an understatement.”

Sam didn’t know what to say. The idea that Dean had finally managed to find someone, no matter who it was, sounded almost too good to be true to Sam. For years, he had firmly believed that Dean was simply too stubborn and lost in self-loathing to even consider an actual relationship as an option.

“What he is like?” he said, fascinated at the idea.

“Cas? Um, he’s kind of difficult to describe. You have to see it to believe it. But I can tell you that he’s loyal. And friendly. A little weird, perhaps, but in a good way. You’ll like him. He’s precious. He’s a good thing for your brother, Sam. Don’t worry. And he needs Dean too. They need each other. The point though,” continued Gabriel, “is that this needs to happen because—um, no offence—but you guys are all kinds of screwed without him. This is a big win for you guys, and especially for Dean. And there’s no way you—we—can manage to succeed if he’s not involved. No way.”

Sam thought for a moment and said, “So Dean gets taken care of by Cas,” which made Gabriel let out a laugh, “and you—you’re really here to…”

“I’m here for you, Sam,” he said, looking almost uncomfortable. “I’m here to help you with Ruby. I hate to say it, but this is where the road of truly crappy things for you begins, Sam. And as unfair as it is, so many other parties are counting on it. So I’m—I’m hoping I can change that.”

“Including the really bad rift between Dean and me that you talked about.”

“It gets fix eventually but…it’s…it’s a large wound I’d like you to skip. Among other things.”

Sam looked down and nodded, absentmindedly. “What else?”

Gabriel remained silent, which made Sam lift his head and look straight at him with an air of defiance. “What else?” he repeated.

“I’m afraid we get the bad end of the deal, you and I.” He scoffed, “All of us really.”

“Like?”

“How does dying and a sojourn in hell sound like to you?”

“Us both?” said Sam, horrified.

“You. For starters. And well, technically, not me, but I—close enough.”

Sam frowned. “I’m—I’m going to go to hell?”

“Not because you deserve it, no. Totally taking one for the team,” he added, trying to lighten the mood, while knowing he absolutely failed.

Sam lowered his head again.

“Which,” said Gabriel, after he cleared his throat, “I would really like to avoid. In the perfect scenario that I’m hoping we can come up with, none of this crap happens.”

Sam swallowed. He didn’t move a muscle, feeling his chest becoming heavier with every second passing.

“Sam, still here?”

He nodded. “And Ruby is responsible for this?”

“As much as I would like to blame it all on her, I suppose I can’t do that. But she is definitely a key element in your demise, yes.”

Sam took a deep breath and walked to the window, mulling everything over. He turned around, his arms crossed over his chest, and looking at Gabriel, he finally said, “What do you suggest we do then? To stop it all?”

An expression of relief spread across the archangel’s face. “This is not going to be easy, and it won’t be done over night. Many phases and planning, I’m afraid, and most of it should only be done once we have Cas and Dean in our corner. I’m hoping we can recruit other team players to our side much earlier this time around too. Myself, for instance.”

“Yourse—what?”

“But the main thing,” continued Gabriel, ignoring his confusion, “that we really need to do for now is ensure nobody gets tipped off about our scheme. No one. Not Ruby. Everything has to seem to be going according to plan.”

“But why? Why all the secrecy?” he specified.

“Because, you beautiful dum-dum, you’re being watched and no one can know I’m here, much less that I’m talking to you. Which is a headache enough as it is, but there were…additional concerns that I had to take care of too. But that’s not important for now…”

Assessing that he had most likely confused Sam even more with his last comment, Gabriel sighed and walked to the table where strong liquor bottles were waiting for him.

“Let me ask you a question,” he said as he poured drinks for the both of them. “Even if you yourself know more than the majority, how can you still win over someone who has access to far more information than you ever could, and has pretty much utter control of the whole game?”

Letting Sam ponder on his question, he quietly walked towards him and sat on the bed beside him after handing him a glass.

Sam sipped on his drink and said, “And they are aware of that fact?”

“Big time. No reason to doubt it.”

“Then I’d used that to my advantage. If they think they know and control most of everything because they do—” he chuckled and took another swig of his drink. “I guess, I’d make sure to make it seem like that never changed so they wouldn’t suspect anything, until an opportunity would present—” Sam paused, shooting a look at an amused Gabriel resting beside him, and then continued, “until an opportunity would present itself, allowing me to do real damage.”

“How _tricky_ of you, Sam Winchester. I’m very impressed and so glad I picked you on my team. But that was my thought exactly. Which is why, when we’re done with tonight’s discussion, after I’ve gone over all the details, you’ll have to go back to Ruby and act like nothing has changed.”

“What?” said Sam, bewildered. “No, but—”

“I’ll keep an eye on you and we will touch base every day, don’t worry. But if we want to keep up with the appearance that everything is going according to plan, I’m afraid it’s more than just me laying low or us sneaking around. That also includes you tagging along with Ruby and appearing…um, jolly to do so.”

And as Sam was about to protest, Gabriel added urgently, “That reminds me.” He held up his finger, signaling Sam to wait a moment. He reached for something into his jeans pockets, then his jacket. “Where did I—oh, here!”  He retrieved a small box from his jacket. He opened it and presented it to him. “Sam Winchester, would you do me the honor,” he said, jokingly, as he revealed a large silver ring with a massive dark stone.

Sam looked at him questionably.

“It’s for your protection,” added Gabriel. “It took me a while to find this beauty. It has been hidden somewhere at the bottom of the sea for centuries. I knew nobody would miss it, which meant no screwing around with the timeline. I made a few additions that should help us out.”

Sam picked up the box and looked at the ring more closely. It had the letter “W” carved into the stone.

“I added that. Purely for aesthetic, of course. Just thought it would make it a little personal, so no one would question you too much about wearing it.”

“Um, what kind of protection?” he asked, still observing the ring.

“Remember what I said about setting up a temporary cone of silence in this very room?” Sam nodded. “Well, hopefully, if I did everything right, this will be your travel sized, far better upgrade.”

Sam shot him a confused look.

“Okay, so, again, nobody can know we’re talking,” Gabriel reminded him.

“Or that you’re here,” added Sam.

“Exactly. And that’s really annoying because, like I said, a bunch of people are keeping tabs on you. And um, not to creep you out, but they are thorough. More than you might think. I could set up powerful protective spells that would keep demons and angels away, even though they are not our only concerns, but none of this matters because you’re not supposed to know about angels in the first place—”

“And that would tip them off.”

“Yeppers. Besides, those kinds of spells can only be set to a location, not a person. And you can’t just stay hidden forever or that will also raise eyebrows.”

“So if I wear this ring, it will…what? Keep me off the grid completely?”

“No. That’s the one I’m wearing,” he said, showing off the ring on his left hand. “I _have_ to keep off the grid, but anyways,” he said, waving his hands around. “What’s important is that you can’t disappear, because that would be unusual. So, um, not that it is the perfect explanation, but you know what selective memory is, right?”

Sam frowned. “Yeah, that’s when you chose to remember certain things and sort of purposely discard others of a particular event or something.” Sam then gasped and looked at the ring. “Are you telling me that if I wear it I’ll forget you or something?” he asked, genuinely upset.

“No, no. I don’t want to wipe your memory, temporary or otherwise. You have to remember.”

“Good,” said Sam, relieved.

“But other people cannot know what you know now.”

“I’m not going to tell them.”

Gabriel laughed. “That’s adorable, Sam. I appreciate the sentiment, and I don’t doubt that you would be able to keep a secret. But some people, demons, angels, or um, other powerful beings, they can get inside your head whether you want it or not. For some, it won’t even be a matter of proximity. They can easily access information from you and you wouldn’t even know.”

“That’s—that’s messed up.”

“Yeah, tell me about it. So far, we’re protected from that because of my…cone of silence whatever in this very room and other spells I had used as good measure, just like I had done so yesterday as well. But I’ve used these twice already now, and I cannot press our luck by attempting this everyday. This is powerful stuff and if you abuse it…. As for when you wandered off earlier today, at best, if people were checking in, they’d assume you had a weird dream. And since I’m doing everything to not be detected, it’s very unlikely that anything remotely similar had happened before. Right?”

Sam nodded and Gabriel continued with a warning tone, “But the moment you’ll leave this room after tonight, even if you don’t tell Ruby or anyone, you’ll be walking around with all the information I’ve given you. Which is far more than what I told you yesterday, and that puts us both and our plan at risk.”

Sam bit on his bottom lip.

“But that’s where the ring can help. I’ve altered it so it would be linked to me. The 2018 me. So, if I’ve done the job properly, when you wear it, every bit of information, memory or anything related to me should be kept hidden from anyone else.”

“So…no more people reading my mind?”

“They will still be able to get inside your head, but they won’t find anything associated with me. Or what I’ve told you. Or our plans. Or the time we spend together. Unless, you voluntarily share it, of course.”

Sam flinched. “I can still talk about it?”

“Of course. You always have a choice. I’m not here to control you. I’m here to help you.”

Sam nodded. He held the ring between his fingers examining it. “Wait, if yours makes you go off grid or something, how I can see you? You’re wearing it right now.”

Gabriel hesitated for a moment, and then said, “I’ve made alterations on mine as well. Similar, but not identical to the way I linked your ring to myself. I linked mine to you.”

Sam held his breath and looked at Gabriel gravely. “You’re saying that my ring is specifically to keep everyone from knowing any memory I have of you, while yours is to ensure that I’m—I’m the only one who can interact with you?”

“Pretty much.”

“That’s—but—you don’t find this depressing? Or lonely?”

“I’ll be fine, Sam. It’s just in the meantime, and honestly, having a lot of peaceful me-time is really not a bad thing considering where I came from.”

Sam was not utterly convinced by Gabriel’s statement, but judging that he wouldn’t be able to do anything about it in that moment, he resigned himself to let the matter rest for now, until hopefully he’d find a better solution.

“Do I just put it on?”

“Yup.”

“No incantations?”

Gabriel shook his head, smiling. “Just, once you put it on, no backsies. Don’t take it off.”

“Obviously, that’s the point.”

“No, I mean, once you take it off, it’s not just that you won’t be protected by it anymore, it will have a counter effect. That’s the price. Mine is the same.” Sam opened his mouth but nothing came out of it, unsure what Gabriel was getting at. “What I mean,” he said, “is that if I take it off, it’s not just that I am back on the grid for anyone who happens to be looking for me. The ring is hiding me, so once it’s off it will then automatically turn me into a beacon. Everyone _will_ know I’m here. And yours—”

“Everyone will be able to access my memories.”

“Bingo.”

“So, no backsies,” repeated Sam. And just as he was about to put it on, he stopped when a worrisome thought came to him. “I don’t usually wear rings. If I can’t take it off, how do I make sure it will fit?”

“The ring’s magic, Sam,” he laughed. “It will fit.”

Sam rolled his eyes and put the ring on his middle finger of his left hand. He held his breath and waited to feel any indication that it worked.

But nothing.

“That’s it?”

“That’s it. _Mazel tov_.”

“Now that I’m officially proofed, we can get to the plan? How is Ruby going to backstab me? How are we going to stop her? And what exactly is their big picture plan?”

“Absolutely. Before we get to that though, there’s one more thing I’d like to discuss with you, Sam,” he said in a gentler tone. Gabriel looked away and hurriedly finished his drink. He repositioned himself and cleared his throat.

Sam observed him carefully, wondering what on earth could make him feel this uncomfortable considering everything he had just told him.

“It came to my attention when I visited you last night,” he finally said, but with his eyes still away from Sam, “that um, perhaps I—we—that, um, we should talk about the Mystery Spot.”

Sam bit on his bottom lip and gave him a short nod, as he slightly twisted himself as well, looking in front of him. “You mean, um, what did you call it? Harsh love?”

Gabriel sighed. “Yeah, that. Um, look, I—I’m sorry.” Sam remained still, but glimpsed at Gabriel at the corner of his eyes for a moment, surprised at his apology.

“I meant what I said,” continued Gabriel, “this was done out of…concern for you. Being an angel, I knew what was waiting for you and Dean. I knew even when you met me back at Crawford Hall. I could tell you were very stubborn, particularly about saving Dean. I mean, you still are and that’s not a bad thing. But the Mystery Spot, you just—you just didn’t stop and that worried me about what would really happen to you once Dean would be gone. Giving what’s happening right now with Ruby and all, I think we can both agree I wasn’t completely far off about that. I was hoping our encounter would have been a wake up call for you that things don’t always work out, and that—well, anyways…” He took a deep breath and Sam could feel his gaze on him. “But, um, I would be lying if I didn’t admit that I let it go further than I should have. And I’m—I’m sorry.”

Sam swallowed and nodded. They both remained silent for a time and Gabriel finally said, “Feel free to yell or whatever it is you need to do. I know I deserve it.”

His voice wasn’t broken or even shaking with fear or sadness, but Sam detected something else in Gabriel’s tone that he couldn’t ignore: remorse. He knew everything he had told him was the truth.

Which made Sam’s uneasiness dissipate a little.

“You scared me,” he said in a low voice, looking down at the glass he was holding. “What you did, it scared me. Not just the part about seeing Dean dying over and over and not being able to do anything about it. But the—the worst part, the really terrifying part of all this was the months after that Wednesday where I thought Dean was really dead. It wasn’t just about me failing to help Dean. It also showed me who I could become without Dean around. A cold obsessive fool driven by revenge.” He swallowed and tightened his grip on his glass. “I remember what it felt like. It still hits me once in while. I was consumed by it. Especially—I didn’t care about anything else. Anyone else. I did things that—” he cleared his throat and looked upwards, fighting down the tears. “My moral compass was out of the window and with that I became a whole other person, and it scared the shit out of me. And it’s—it’s happening again.”

“I’m so sorry, Sam. I was trying to make you understand—to warn you that you can’t control everything. But that doesn’t mean you have to give up on yourself. And to see you here, still struggling anyway…what a colossal waste of our time and wits. Evidently I should have taken a kinder approach, no arguments there. I was kind of an asshole. An asshole who meant well, but still.”

Sam let out a faint laugh and turned to Gabriel to look at him at last. Seeing him with apologetic and pleading eyes meant a lot to Sam. And just like that, he felt his whole being become a little lighter as he decided that he was no longer angry with him anymore. With a warm smile, Sam said something he never thought he would say to him, “Thank you for telling me. And I forgive you.”

Gabriel flinched. “You’re welcome,” he said unsure. He stared at Sam and said, “That’s it? No ‘how dare you?’ or ‘keep dreaming’ or I don’t know, angst and resentment? What I did was horrible, I told you I deserve it.”

Sam smiled at the corner of his mouth. “Gabriel—Gabe, I—can you I call you Gabe?” He nodded. “Gabe, I—I’ve been angry for months now. Well, years, if I’m completely honest…and it’s killing me.” He sighed. “And you coming here, telling me Dean will be okay, that we can all be okay…I don’t want to be angry anymore. I don’t want to feel helpless and—I just—I don’t want to be this person. You apologized. And you really meant it, which is rare enough to get from someone. And you’re here to help me. To help us all. And from what I understand, you didn’t have it easy on your end either. Coming back here, taking a chance and not knowing how I would react, it’s not nothing. Actually, it’s everything.”

“That’s—thank you, Sam.”

“And I’d like to put this behind us once and for all if we want to move forward like you said.”

“You’re sure?”

Sam nodded.

Gabriel took a massive breath of relief. “All right. But Sam, if you, um, if for whatever reason you ever feel like you need to revisit this topic…”

“I’ll tell you. I don’t think I will, but I’ll tell you.”

“Good,” said Gabriel with a firm nod.

They stared awkwardly at each other.

“Should we shake on it or hug? I feel like this is weird now.”

They laughed nervously, both remaining still as Sam tried desperately to keep his eyes away from Gabriel while he was suddenly focusing on fixing his jacket for some reason.

“So,” said Gabriel, desperately seeking to kill the silence, “want me to tell you how we’re going to take the bitch down and all the other assholes who mean to ruin our lives too?”

**Notes for the Chapter:**

> Thank you to Danica and Landrala for your help and support!
> 
> and thank you for reading!! I'm sorry it took so long to post the next chapter, but I hope you enjoy it nonetheless :D

**Author's Note:**

> This is my first attempt to (alternate) Canon :)  
> Thank you to Landrala and Danica for your help and support!!!
> 
> Hope you enjoy it and thank you for reading:)


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